Snowbirds love to fly away from cold winter weather in the middle of the season. No one wants to stick around under gray skies, all layered up in heavy coats, boots, and scarves. Of course, folks who are lucky enough to book a trip to a sunny getaway in January or February still have to worry about what to wear. All of their summer clothes are stowed for the season, and no one wants to wear something old on holiday, anyway. The best women’s fashion boutiques know that it’s smart to offer out-of-season clothing in the middle of winter. The snowbirds are happy to snag warm-weather items that can then transition to spring and summer. Peek at the most versatile pieces of resort wear. Find out what outfits are essential for wintertime vacations that take place in summertime climates.

Crops for Vacation

Cropped pants, capris, clam diggers—whatever you call them, they’re the perfect pick for a winter spent in a sunny spot. A shop that keeps its racks and shelves stocked with cropped pants will always sell out, even during colder months. They’re staples in the spring, summer, and fall because they transition between seasons with ease. It’s not a stretch to place them front and center in winter, either. For those vacations in Florida, trips to New Zealand, or Caribbean cruises, they’re a hands-downs fave.

Captivating Caftans

To rock a breezy summertime look in the middle of winter, caftans are killer. They’re more substantial than swimsuit cover-ups and, in a pinch, a stylish caftan can do double-duty as a dress. Throw on some sandals, and it’s an effortless go-to ensemble for dinner by the water or an evening walk along a balmy boardwalk. Stores that specialize in resort looks know the importance of displaying caftans all year long. The key is to keep an eye out for caftans with jaw-dropping details, such as sequins, embroidery, or beadwork. A mix of long and short pieces is best. A shorter caftan is too cute, and tends to take on a retro-inspired mod vibe.

Romping in Rompers

 Romping in Rompers

Rompers are the darlings of the resort set. A romper offers a complete outfit in one go. It cuts down on packing, erasing the need to fit half a dozen pairs of shorts and matching tops in the suitcase. Furthermore, some rompers are downright fancy. The versatile items can appear quite stunning, given the right color palette and design. Basic black goes from day to evening without a care, but a warm getaway in wintertime begs for bright colors and eye-catching prints, as well.

Scarves Galore

Forget about the cozy knit scarves that folks need to survive the winter. A sunny holiday requires flowing, lightweight scarves. They’re unbeatable accessories, not only because they’re vivid, but also because they’re fantastic statement pieces. A light scarf can go over the hair, around the neck, around the waist as a belt, or tied around the hips. The best part is that they work in the winter in any locale, although it’s often necessary to wear more than one.

Sensational Footwear

 Sensational Footwear

It’s impossible to take a winter vacay to paradise with a bunch of boots and snowshoes. Women’s fashion boutiques that offer sandals, flip-flops, and other summertime must-haves all throughout the year will quickly become the hot-spot for holidaymakers. Summer shoes take up less space in the suitcase, plus a pair or three is all that’s necessary for most vacations. However, the transition from one climate to another calls for shoes that are more substantial than a pair of thongs, so sneakers might be in order, too.

The Beachwear

The Beachwear

Who doesn’t want to swim in a hot, sunny climate? Resort season creates a new swimsuit season, but it’s worth it to swim in the ocean or lounge by the pool. Far too many stores put away their bikinis and one-pieces toward the end of summer, and they don’t show up again until spring. It’s wise to take advantage of snowbirds flying south in the winter because it represents an upwardly mobile new niche of shoppers in need of bathing suits and cover-ups.

Can’t-Miss Accessories

In addition to scarves, travelers need a slew of additional accessories to complete their warm weather ensembles. It’s easy to find sunglasses throughout all seasons, so picking out statement shades is rarely a problem. Just because it’s cold and gray back home doesn’t mean it’s okay to skip out on the sun safety on vacation, though. It doesn’t hurt to take a sun hat to bright, baking-hot locations. Layering jewelry and other accent pieces can add refined flair to beachy outfits.


There’s nothing more relaxing than lounging away in a sunny spot, especially when it’s freezing back home. As always, however, it’s crucial to dress with for the occasion. What other summertime staples ought to go on the packing list for a wintertime vacation?

Guest Author Bio: 

Cassandra is a fashion writer and content strategist. She specializes in collaborative branding efforts with up-and-coming designers and fashion companies.